US2212959A - Photoprinting process - Google Patents
Photoprinting process Download PDFInfo
- Publication number
- US2212959A US2212959A US251338A US25133839A US2212959A US 2212959 A US2212959 A US 2212959A US 251338 A US251338 A US 251338A US 25133839 A US25133839 A US 25133839A US 2212959 A US2212959 A US 2212959A
- Authority
- US
- United States
- Prior art keywords
- compound
- light sensitive
- parts
- diazo
- sensitive material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title description 4
- 239000000463 material Substances 0.000 description 24
- 150000008049 diazo compounds Chemical class 0.000 description 17
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 13
- 230000008878 coupling Effects 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- -1 alkyl radical Chemical class 0.000 description 5
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- LKTJGLDNQVPISM-UHFFFAOYSA-N 1,3-dihydrobenzo[e]benzimidazol-2-one Chemical class C1=CC=CC2=C(NC(=O)N3)C3=CC=C21 LKTJGLDNQVPISM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- KTCBLMXNWYGCRT-UHFFFAOYSA-N 1-[2-(1h-indol-3-yl)ethyl]-3-methylthiourea Chemical group C1=CC=C2C(CCNC(=S)NC)=CNC2=C1 KTCBLMXNWYGCRT-UHFFFAOYSA-N 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- NIPLJYYBLXKSOS-UHFFFAOYSA-N 2-methylnaphthalene-1,6-diol Chemical compound C1=C(O)C=CC2=C(O)C(C)=CC=C21 NIPLJYYBLXKSOS-UHFFFAOYSA-N 0.000 description 1
- UUWREYOLKGVJIN-UHFFFAOYSA-N 2-n-benzyl-2-n-ethylbenzene-1,2-diamine Chemical compound C=1C=CC=C(N)C=1N(CC)CC1=CC=CC=C1 UUWREYOLKGVJIN-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000329 aluminium sulfate Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 235000011128 aluminium sulphate Nutrition 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ZNVGYHOBTCWGTO-UHFFFAOYSA-N solutin Natural products Cc1cc(O)cc2OC(C)(O)C(=O)c12 ZNVGYHOBTCWGTO-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- RHZZVWTVJHZKAH-UHFFFAOYSA-K trisodium;naphthalene-1,2,3-trisulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(S([O-])(=O)=O)=C(S([O-])(=O)=O)C(S(=O)(=O)[O-])=CC2=C1 RHZZVWTVJHZKAH-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/58—Coupling substances therefor
Definitions
- the invention relates to diazo-photoprinting processes and more particularly to light sensitive materials useful for diazotype purposes.
- Diazo photoprinting processes have to fulfil a series of requirements'regarding' the stability and light sensitiveness of the light sensitive materials used as well as regarding the properties of the finished pictures such as stability to water, to storing and to light. These properties of the light sensitive materials and the pictures prepared thereby depend partly upon the azo-components used. The number of known azo-components which practically enter into'oonsideration for making diazotypes is only small.
- hydroxynaphthoimidazoles are very useful azo-components for making diazotypes. They allow of preparing prints which are very fast to light and stable to plied on a support, preferably together with ami-- nodiazo-compounds of the benzene series, particularly tertiary 'para-aminodiazo compounds,
- the new 'azo-components can also be used in developing solutions for wet de veloping in so far as they are sufliciently soluble in water or alkaline solutions respectively. They are, however, principally suited for the preparation of photo-printing papers which can be de veloped with. ammonia gas.
- the naphtho-1'.2':4.5-imidazoles substituted in the naphthalene nucleus by 1 hydroxy groups especially the beta-mono-hydrew-compounds.
- amassin e s droxy'naphtho-1'2':4.5 imidaaole is well suitable.
- the new azo-components may contain further. usual substituentsin the naphthalenenucleus in 1 so far as the solubility of the sac-components is notdisadvantageously aflected thereby. "For in- I ,5 stance, alkyl groups or chlorine enter intoquestion. Preferably, compounds are used, however,
- the azo-componentsu'sed according to the 15 present invention maybe prepared in the usual manner, for instance, by reaction of-diaminonaphthols with formic acid, acetic acid, propioni acid, succinic acid or the like.
- a suitable photoprinting material isobtained by spreading on paper a solution of 40 parts of .citric acid, 30 parts of boric acid, 40 parts of sodium naphthalene-trisulfonate, 50
- azo-component instead of the azo-component mentioned there may also be used with a good'success the 2 ethyl 6 hydroxy- ,aminobenze'ne, 2 parts of tartaric acid, parts of tl iit'mrea and 1.5 parts of the hydrochloride of 2 carboxyethyl '7' hydroxynaphtho 1'.2':4.5-i midazole are'dissolved in 100 parts of water.
- the light sensitive material prepared by means thereof is suitable for the preparation of 'photoprints by developing with ammonia gas after exposure. 1
- diazo-compound from l-diethy amino-4-amino-benzene there may be used corresponding quantities of-the diazo-compound of 1-hydroxyethyl-ethyl-amino-4-aminobenzene.
- Light sensitive material consisting of a sheet support carrying a light sensitive diazo compound and as coupling component a hydroxynaphthoimidazole compound.
- Light sensitive material consisting of a sheet support. carrying a light sensitive diazo compound and as coupling component a hydroxynaphtho-1'.2':4.5-imidazole compound.
- Light sensitive material consisting of a sheet support carrying a light sensitive diazo compound and as coupling component a fl-hydroxynaphthoimidazole compound.
- Light sensitive material consisting of a sheet support carrying a light sensitive para-aminodiazo compound and as coupling component a p hydroxynaphtho- 1.2':4.5 imidazole compound.
- Light sensitive material consisting of a sheet support carrying a light sensitive para-aminodiazo compound and as coupling component a fi-monohydroxynaphtho-l .2 :4.5-imidazole compound.
- Light sensitive material consisting of a 'c'ellulosic sheet support carrying a light sensitive para-dialkylaminodiazo compound and as coupling component a 7'-monohydroxynaphthol'.2' :4.5-imidazole compound.
- Light sensitive material consisting of a cellulosic sheet support carrying a light sensitive para-dialkylaminodiazo compound and as coupling component a 6-monohydroxynaphthol'.2 :4.5-imidazole compound.
- Light sensitive material consisting of a. paper carrying the diazo compound of paraamino-N-diethylaniline and as coupling component the 7'-hydroxynaphtho-1.2:4.5-imida zole.
- Light sensitive material consisting of apaper carrying the diazo compound of paraamino-N-diethylaniline and as coupling component the 6-hydroxynaphtho-l'.2:4.5-imidazole.
- Light sensitive material consisting of a paper carrying the diazo compoimd of paraamino-N-diethylaniline andas coupling component the 2l-methyl-7'-hydroxynaphtho-1..2':4.5- imidazole.
- Light sensitive material consisting of a sheet support carrying a light sensitive diazo compound and as coupling component a hydroxy- 1'.2':4.5-imidazo1e compound the imino group of which is unsubstituted.
- Light sensitive material consisting of a sheet support carrying a light sensitive paraaminodiazo compound and as coupling component a fl-monohydroxynaphtho-l.2:4.5-imidazole compound having an alkyl residue in .the
- MAXIMIL I AN PAUL SCHMIDT. OSKAR SUS.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE210212X | 1938-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2212959A true US2212959A (en) | 1940-08-27 |
Family
ID=5796178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US251338A Expired - Lifetime US2212959A (en) | 1938-01-26 | 1939-01-17 | Photoprinting process |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2212959A (en)) |
| BE (1) | BE431763A (en)) |
| CH (1) | CH210212A (en)) |
| FR (1) | FR849407A (en)) |
| GB (1) | GB523922A (en)) |
| NL (1) | NL49311C (en)) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2537097A (en) * | 1945-08-18 | 1951-01-09 | Gen Aniline & Film Corp | Dyeing of textile materials by the use of light-sensitive diazo salts |
| US2548845A (en) * | 1948-12-16 | 1951-04-10 | Gen Aniline & Film Corp | 4-hydroxy-2-alkylbenzimidazoles as azo coupling components in diazotypes |
| US2618555A (en) * | 1949-04-09 | 1952-11-18 | Kalle & Co Ag | Process for positive diazotype and negative metal reduction images and light-sensitive material therefor |
| US3140181A (en) * | 1960-08-03 | 1964-07-07 | Grinten Chem L V D | Water-fast two-component diazotype paper |
| US3910794A (en) * | 1972-04-20 | 1975-10-07 | Cellophane Sa | Imidazole couplers for two component diazotype systems |
| US4225662A (en) * | 1978-04-14 | 1980-09-30 | Ricoh Company, Ltd. | Diazo copying material |
-
0
- NL NL49311D patent/NL49311C/xx active
- BE BE431763D patent/BE431763A/xx unknown
-
1938
- 1938-12-14 CH CH210212D patent/CH210212A/de unknown
-
1939
- 1939-01-17 US US251338A patent/US2212959A/en not_active Expired - Lifetime
- 1939-01-17 GB GB1637/39A patent/GB523922A/en not_active Expired
- 1939-01-25 FR FR849407D patent/FR849407A/fr not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2537097A (en) * | 1945-08-18 | 1951-01-09 | Gen Aniline & Film Corp | Dyeing of textile materials by the use of light-sensitive diazo salts |
| US2548845A (en) * | 1948-12-16 | 1951-04-10 | Gen Aniline & Film Corp | 4-hydroxy-2-alkylbenzimidazoles as azo coupling components in diazotypes |
| US2618555A (en) * | 1949-04-09 | 1952-11-18 | Kalle & Co Ag | Process for positive diazotype and negative metal reduction images and light-sensitive material therefor |
| US3140181A (en) * | 1960-08-03 | 1964-07-07 | Grinten Chem L V D | Water-fast two-component diazotype paper |
| US3910794A (en) * | 1972-04-20 | 1975-10-07 | Cellophane Sa | Imidazole couplers for two component diazotype systems |
| US4225662A (en) * | 1978-04-14 | 1980-09-30 | Ricoh Company, Ltd. | Diazo copying material |
Also Published As
| Publication number | Publication date |
|---|---|
| BE431763A (en)) | |
| FR849407A (fr) | 1939-11-23 |
| NL49311C (en)) | |
| CH210212A (de) | 1940-06-30 |
| GB523922A (en) | 1940-07-25 |
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